


The terribly wonderful life of Dean Winchester

by woahhsailor



Category: Supernatural
Genre: Alternate Universe, Blow Jobs, Boss/Employee Relationship, Deepthroating, Drunk Castiel, Drunk Dean, Drunken Kissing, Drunkenness, Hand Jobs, M/M, Masturbation, Masturbation in Shower, Public Blow Jobs, Public Display of Affection, Public Hand Jobs, Shameless Smut, Smut
Language: English
Status: Completed
Published: 2016-01-09
Updated: 2016-01-09
Packaged: 2018-05-12 18:45:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,032
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5676646
Author URL: https://archiveofourown.org/users/woahhsailor/pseuds/woahhsailor
Summary: <blockquote class="userstuff">
              <p>The man’s dress shirt was stretched across his shoulders and it tucked seamlessly into the waistband of his belted slacks. When his boss’s hands slid into the pockets of his dark blue pants, Cas had to swallow a lump in his throat as he watched his pants pulled tighter against his round behind.</p>
            </blockquote>





	The terribly wonderful life of Dean Winchester

**Author's Note:**

> Biggest shout out in the world to @shissouchan. Without you this fic wouldn't have happened. Thank you so so much for listening to me bitch, helping me and of course being a great beta while I panicked.

“Castiel, we need to know if you’ll be bringing a ‘plus one‘ to the company party tonight,” his boss asked him politely. He’d never had more than two conversations with the man because he always sat in his office on the top floor of the building. Castiel saw him almost daily while he went on coffee runs or, if the boss-man decided to leave early, he’d see him in the elevator.  But one of the biggest names in the city talking to him face-to-face made him nervous.    
  
It probably didn’t help the ‘lowly’ office worker that his boss was absolutely  _ fucking _ gorgeous. He was slightly short for Castiel’s ‘type,’ but he figured it was from his permanently bowed legs, which Cas had never found sexier in his life. Plus, today he was wearing this blue and white vertically striped dress shirt with white cuffs and a white collar which made him look so much taller than he was, paired with the sexiest pair of suspenders he’d ever seen in his life. And, the red silk tie around his neck made Castiel itch. He wanted nothing more than for his boss to ride him after he’d knotted the tie around his wrists.   
  
“Sir, more than likely I will be on my own. My apologies for not relaying that information sooner,” Castiel replied to the man, the two of them standing outside of his cubicle. Castiel was just fixing to leave for the afternoon, his work all stacked away neatly in his briefcase to be finished at home. He’d come in on a Saturday afternoon to finish up an expense report, knowing that his boss would be here working over as usual. He hadn’t expected to talk to him, though and now he’d have to go home get ready for the party,  _ go _ to the party he dreaded, and then go back home to finish some extra work.     
  
“Thank you, Mr. Winchester,” Castiel replied, nodding his head as his boss turned to walk to the elevator. Cas followed a few steps behind. He’d purposefully waited for the other man to go first so that he could watch his ass out to the parking lot. They awkwardly stood in the elevator as Cas attempted to hide the fact that he was eye fucking his boss.    
  
The man’s dress shirt was stretched across his shoulders and it tucked seamlessly into the waistband of his belted slacks. When his boss’s hands slid into the pockets of his dark blue pants, Cas had to swallow a lump in his throat as he watched his pants pulled tighter against his round behind. Cas couldn’t stop thinking about how his bowed legs would look while he slammed into him from behind.    
  
Cas had to adjust himself through his pocket when the elevator finally dinged and opened on the first floor. He followed his boss out to the parking lot where only two cars sat: a black hard top 4-door ‘67 Chevy Impala in pristine condition, and a little silver Nissan Altima. Cas slide behind the wheel of his little silver car and watched through the windshield as Mr.  Winchester pulled out of the parking lot in his classic car.    
~~~~~~   
Castiel had barely waited for his front door to click closed before he started to strip his work clothes off whilst walking to his bathroom. He left a trail across his living room and down his hall. He was completely naked when he hit his downstairs guest bathroom. As he waited for the water to warm up in the shower, he feathered his fingers down his length, from tip to base. He shivered from the sensation, already half hard from the thoughts at work.    
  
When the shower was warm enough, he stepped into the steady warm stream, letting it fall over his half erected cock. Castiel reached down and wrapped his hand around himself. Slowly, he pulled his hand down till his fist hit his base and then he pulled back up. He shuddered as he thought of pushing himself into his boss' tight hole. He tightened his grip on his dick and pounded against his fist, matching his thoughts of pounding into Mr.Winchester.    
  
He gasped softly while the water showered over his naked body. He quickened his pace, slamming his hand down his cock, thinking about his boss shouting his name, and finally found relief as he shot hot streams of cum onto his stomach at the thought of cumming into Mr. Winchester’s tight ass.  After Castiel calmed down and regained feeling in his legs, he stood directly in the stream of the shower, letting the thick white liquid run off of his torso. Quickly he filled his palm with 2-in-1 body wash and lathered his hair first, and then ran his hands down his torso making sure he left no evidence of his fun. He finished lathering his body before stepping back into the stream.    
  
As the water washed over him, he reminded himself that he  _ had _ to quit doing this. No sane man would cum to the thought of fucking his boss. It couldn’t be natural, he thought to himself. After he was sure he was completely cleaned up he turned the water off and stepped out of the shower. He took a deep breath before toweling himself dry. He  _ really _ did not want to have to face his boss after this.   
~~~~~~~~   
As Castiel entered one of the most lavish and expensive buildings in the city, he thought he might faint. He knew this was a formal event but looking around he immediately felt under dressed. He didn’t have anything nicer than a normal black tux, and he’d covered it with a tan trench coat. As he passed a reflective piece of art he noticed he’d even put his damn tie on backwards.    
  
He muttered a curse before one of the workers quickly ushered him through the doors of a ballroom. ‘A ballroom?’  ‘ _ Yeah.  _ Definitely _ underdressed, _ ’ he thought.. As the man quickly pushed Castiel through the doors he sighed deeply. He did not want to be here after he just yanked it to images of the man who wrote his checks. He looked around at all of his fellow co-workers and even saw some people he didn’t know. ‘ _ This is not going to be fun _ .’ He thought sourly, and as a man walked by with a tray of drinks he snatched one off and downed it in one gulp. ‘ _ If I’m gonna be here _ ,’ He thought,  _ ‘I’m gonna be  _ drunk.’ He breathed deeply looking for another drop of alcohol, but before he found one, his boss caught his eye.   
  
Castiel felt his jaw hit the floor in front of him, and he was sure he looked like one of those “ahooga” cartoon characters. Mr. Winchester was wearing a maroon suit, layered on top of a flattering black dress shirt and a black pocket square. Cas thought he might actually faint at the sight of the maroon slacks stretched over his thighs and -- Cas gulped--  _ bulge _ . 

 

‘ _ Alright, I’m getting hammered, _ ’ Castiel thought grabbing a glass of wine and downing it.    
\----------------------------------------------------D----------------------------------------------------------------------   
  
Dean Winchester had never realized just how attractive the guy who filled out most of his paperwork was until he talked to him after work today. Dean didn’t think he’d even noticed the other man before.  _ How could I have not noticed him before _ ? He was simply beautiful; his hair was the colour of a raven’s feathers and he had sapphire eyes that resembled the bottom of the ocean-- mysterious, and... _ intriguing _ . That man was the kind of beautiful that made Dean Winchester want to start leaving his office.    
  
Dean could see his eyes from across the room, and all he wanted to do was approach him. He couldn’t do that though, First of all because he was his boss. Secondly,he had  _ no idea _ if Castiel even liked men--let alone him-- and he didn’t even _ know  _ the man. All Dean knew was that he needed to go talk to him. He grabbed two glasses of wine off of a passing server’s tray and made his way across the room to the dark haired man.    
  
“Mr. Novak, care for a Cabernet?” Dean asked jovially, holding the win out to the other man. Hesighed happily when the other man reluctantly took the glass from his hand. “Are you enjoying your time here, Mr. Novak?”    
  
“Castiel, please call me Castiel.” The dark haired man replied slowly, “It’s not exactly my scene, but...” Cas trailed off, shrugging his shoulders. For a man who wasn’t so much into the ‘scene’ however, he did seem awfully relaxed. Dean noted this, and tucked that tidbit of information away in his head for later.   
  
“Castiel, has anyone ever told you that your eyes are the colour of Forget-Me-Nots?” Dean asked coyly. He expected it to throw his subordinate through a loop, and he’d likely deem it successful. The sudden stall in speech-- a slight hitch of breath-- the flush across his cheeks; Touchdown.     
  
Castiel chuckled lightly at the compliment, covering quickly, and regaining an indifferent demeanor, “Ah, no that’s a new one, but thank you, sir.” Castiel responded. He was more than efficient at playing the humble paper-pusher-- but Dean be  _ damned _ if there weren’t a twinkle in that man’s eye-- so help him, God!    
  
There was small talk--not at all unpleasant-- and many more glasses of red wine before Dean had that warm tingly feeling that was starting to consume him. He’d be a liar if he tried to say that he wasn’t-- at the very  _ least _ \-- quite tipsy. How many glasses had the two had, now? 

 

There was a lull in conversation-- it felt like ten minutes of silence-- before Dean spoke suddenly, “Hardly working, or am i hard?"

 

As soon as the words fell out of his mouth, both men dissolved into a fit of giggles.    
  
“Well,  _ are _ you?” Castiel asked with a wiggle of his eyebrow.   
  
Dean looked down at his crotch questioningly. “Nope.” he replied with a chuckle and a shrug.   
  
“Do you wanna be?” Castiel replied with words that were just a little soft around the edges.  The wine was now in full effect.    
  
“Care to do the honor?” Dean asked, resting one hand on the other man’s hip before looking around nonchalantly and noticed that  _ most _ but certainly not  _ all _ of the patrons had trickled out. When Dean turned back to the raven-haired man he felt his chest flutter lightly. He was blushing. Castiel was blushing. Something washed over Dean that he couldn’t describe when he saw the red tint covering the other man’s face. Dean was wondering if Castiel would ever answer, or if he’d perhaps overstepped a boundary. That thought was immediately hushed as Castiel crushed his lips against Dean’s.   
  
Dean felt Castiel pull back slightly, lightening the kiss once Dean had wrapped his arms around the other man’s waist. He felt a soft moan escape his throat as his subordinate wrapped his arms around Dean’s neck and lick at his lips all in the same fluid motion. Dean let the other man into his mouth, biting back a moan at his their tongues slid together softly. It took all of his strength, but the boss-man finally pulled himself away from the kiss.    
  
“Come with me,” Dean told Castiel, his voice husky and serious as he grabbed the raven haired man’s hand and led him across the room and down and empty hallway. Once in the empty hall Dean let Castiel push him against a wall, intent on resuming the kiss from earlier. He felt the other man slip his thigh between his bowed legs and Dean braided his fingers in the dark hair in front of him. Dean let Castiel hold both of his wrists, pinning his arms above his head with only one hand, his head lolling back slightly in pleasure.   
  
Castiel took this opportunity to press kisses from Dean’s now scruffy jaw, down to his collarbones, causing a low guttural sound to escape from Dean’s lips. Dean felt his hips automatically roll up against the other man’s thigh, brushing his half erect cock against him. 

Dean let the other man slide his hands up his torso under his jacket and shit, Cas’ cold fingers feathering across Dean’s skin caused Dean to shudder and pull back.    
  
Before Dean could dive back in, he watched the other man’s head snap to the side. 

 

‘ _ Footsteps _ ’ Dean thought, and without thinking he pulled his wrists loose and grabbed Castiel’s hand and pulled him into a nearby coat closet. He turned the knob slightly so that it didn’t click when he shut it. He suddenly felt oddly sober considering that between the two of them they drank most of the wine bar.    
  
Something about this experience shot adrenaline and lust through Dean’s body, and after the footsteps passed the door they were hiding behind, he loosened his belt and top button before pulling Castiel back in for a kiss by wrapping his arms around his neck. This time the kiss was softer and less feverish, a shared moment between the two in the empty closet.    
  
\-------------------------------------------C-------------------------------------------   
  
Castiel slipped his hand between the two of them, working at the buttons on Mr. Winchester’s jacket soon it was sliding to the floor. While he pressed soft kisses against the other man’s lips, he could feel his hands wandering, like he was trying to read braille off of his superior’s body.    
  
“You don’t know how long i’ve been waiting to do this.” Castiel whispered breathlessly before grabbing Dean by his hips and pulling their bodies close together.

  
“To do what exactly?” Dean asked, his voice graveled over with lust.   
  
“This.” He responded before sliding his hand between his boss’ slacks and silk boxers, noting that he was definitely bigger than his bulge had even suggested. Dean choked back a moan, feeling the other man through the thin material. He was already rock hard by that point, and his tip had begun to leak pre-cum onto his slick boxers. Before he could stop himself, he started rocking his hips against Castiel’s open hand letting him palm him over the fabric.    
  
Castiel heard the other man moan, his head lulling back giving him the opportunity to lick Dean from his collarbone to his earlobe. He could feel Dean’s string of curses through his tongue on his neck and it shot a shiver down his spine. Castiel took a leap of faith and slipped his hand under his boss’ boxers and wrapping his hand loosely around the head of his throbbing cock, waiting for a response.    
  
When he saw that Mr. Winchester wasn’t going to stop him, he tightened his grip, rolling his palm around his tip. The precum covered his palm in a thin layer. Using the other man’s natural lube he stroked him softly down to his base, causing Dean to let out a guttural moan.

 

“Do you like that, Mr. Winchester?” He whispered against the other man’s ear.    
  
“Y-yes” He managed to reply, breathlessly, while Castiel caressed his length.    
  
Castiel continued to stroke his higher’s cock-- starting out slowly, and gaining speed the more the other man’s breathing quickened. Soon, the only sound filling the tiny coat closet was the sound of slapping skin and dirty moans. Cas dipped his fingers down to feather over the sensitive skin of his partners manhood, tucked tight underneath his cock. Castiel smirked at the thought that’d be making his boss cum soon just from his hand.    
  
Cas dropped to his knees in front of the man, it was too dark to see his face, but he could hear Winchester swallow hard. He feathered his fingers across his boss’ waist just slightly teasing the skin above his unbuttoned slacks. Cas leaned forward and pressed a kiss just above where the belt buckle had previously sat, and pulled the other man’s maroon suit pants down around his knees.    
  
He wrapped his hand firmly around the base of Dean’s cock before teasing the tip of the man’s throbbing cock with the end of his tongue. When he felt his boss grab at his hair, he knew he was doing something right. He wrapped his free hand around to hold the back of Dean’s upper thigh and using just the very tip of his tongue, ran up Dean’s length from his base to the very tip, causing the other man to bit back a groan and pull on Cas’ hair.    
  
“Please,” Dean asked, his husky voice full of lust rang out in the dark coat closet.    
  
And with that, Cas brought his boss’ cock completely into his mouth, letting his head hit the back of his throat all in one fluid motion. His superior gasped a curse out loudly, momentarily forgetting that they were actually hiding. While Castiel was sucking his partners dick, he let his hand and mouth meet together so no part of his length was untouched. As the man writhed under Cas’ control, he decided he’d let him cum.    
  
He moved both of his hands, holding on to the other man’s firm ass and pushed his entire length into his mouth once again, letting Dean slide into his throat. He slowly pulled back sucking down the other’s complete length until his dick came out of Cas’ mouth with a ‘pop!’. Quickly, he sucked his boss’ cock back into his mouth and bobbed his head.    
  
It took three complete base to tip sucks until Dean grunted out between throaty gasps. “I’m gonna - I’m, C-Castiel, I’m!” Castiel ignored the cry and continued until the other man pulled his hair hard enough that he forced his dick back into Cas’ throat. As Dean felt the back of Cas’ throat against the tip of his cock he couldn’t hold back anymore and he came. Hot shots of  _ fucking paradise _ shot straight down his employee’s throat.    
  
Castiel finished Dean off by sucking him dry, before swallowing hard. With that, he stood, wiping at the side of his mouth casually. There was a momentary pause before he adjusted his suit and, facing his boss in the tiny dark room, said,   
“Uhm, so, lunch in your office on Monday?” 

**Author's Note:**

> shipsandshit.tumblr.com


End file.
